Princess Eugenie's Most Inappropriate Outfits So Far

Times have been undoubtedly complicated, to put it mildly, for Princess Eugenie, whose parents, former Prince Andrew and former Duchess of York Sarah Ferguson, were stripped of their royal titles and dwellings in October 2025. But Eugenie and her older sister, Princess Beatrice, put on a brave face as they found support with the royal family at Sandringham over Christmas later that year. For the event, Eugenie wore a plaid coat, which royal watchers seemed to approve of, but one element didn't feel quite right: her bare arms. At one point, she was photographed pulling her arms up into her sleeves, presumably to warm them. Her cousin Prince William's wife, Catherine, Princess of Wales, donned gloves, so we're not sure why Eugenie didn't as well.

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This, however, isn't one of her most inappropriate outfits. Like Princess Beatrice's most inappropriate outfits, some of the following looks broke royal protocol, while others missed every style cue in the book. For the most part, though, Eugenie seems to be improving her style. She even attended Paris Fashion Week in 2024 and seems to be dressing her figure more favorably as well. At least a few things are looking up for Eugenie.

In March 2009, Princess Eugenie joined her sister and mother at the world premiere of "The Young Victoria" in London. We get that she was likely doing a "support British designers" thing by wearing a Temperley London dress and Jimmy Choo heels, but the whole muddled mess felt inappropriate for the then-18-year-old. The studded rocker shoes were too heavy for the nightgown-like dress, which blew up in the wind, showing a lot of leg and nearly exposing her.

Prince William and Kate Middleton's 2011 nuptials remains one of the biggest weddings of the 21st century so far, but what did Princess Eugenie decide to wear to the occasion that had millions of global viewers? A blue bomb that landed her on the list of worst-dressed royal wedding guests ever. As we've repeatedly said, it's inappropriate for wedding guests to wear over-the-top outfits that distract from the couple, and unfortunately, Eugenie's ridiculously tall hat, tucked-under hemline, and cringe-worthy top achieved exactly that. At least Beatrice's look was in a muted color and more streamlined.

A quick glance at Princess Eugenie's outfit for her King Charles' 2023 coronation might have you exhale with relief: a sensible navy-blue ensemble with a not-too-ridiculous hat on top. But then we reach the shoes. Don't get us wrong — her invisible-heel Fendi mules are incredible statement footwear. But critics immediately counted this among the worst looks at King Charles' coronation, citing the inappropriateness of the open toe for the church ceremony, but also calling the shoes risky for someone who's pregnant, which the princess was at the time.

Tut-tut, Princess Eugenie. The teenager showed up to the Royal Ascot racecourse in June 2008 in a rule-breaking outfit. The annual races are possibly more renowned for the fashion than the horse racing, and just as equally known is the strict dress code. Although the rules are reportedly updated annually, modesty is always on the agenda, and sheer fabric is forbidden for those sitting in the royal box. Sadly, this is why the princess' bust-revealing sheer dress is one of her most inappropriate outfits.

For a reception at the 2018 Commonwealth Youth Forum in London, Princess Eugenie wore what looked like a cute outfit with a floral Whistles dress and suede knee-high boots from Isabel Marant. But it still ruffled feathers, as some folks found it too short for a royal event. One onlooker commented on Facebook, "Royals tend to have a higher standing and dress code to live up to. It looks nice, but depending on the event, the Queen might think it's too short."

Wearing something wrinkled — no biggy, right? No one's dying because we're not perfectly pressed. But here's the thing when you're a member of Britain's royal family at a formal event: You need to bring your A-game or the criticism will rain down. That was the case when Princess Eugenie wore a wrinkly Suzannah dress for Queen Elizabeth's Diamond Jubilee in London in 2012. Anything sloppy could have been interpreted as a sign of disrespect toward the crown, which is why this look has landed on the inappropriate list.